HCID 11508119, compound → HCID 11507631, compound

HRID 1241931Notes

Reaction equation

HRID 1241931 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][C:10]=2[N+:22]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C1COCC1.[Pd]>[CH:1]1([CH2:7][NH:8][C:9]2[C:10]([NH2:22])=[CH:11][C:12]([NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 11508119HCID 11508119, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11507631HCID 11507631, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N1-cyclohexylmethyl-2-nitro-N4-phenyl-benzene-1,4-diamine (0.06 g, 0.18 mmol) in THF (5.00 mL) was added 10% palladium on activated carbon (60 mg). The reaction flask was equipped with a septum and was placed under vacuum for 3 min. The flask was then placed under hydrogen atmosphere (balloon inflated with hydrogen) and the reaction mixture was stirred for 16 h. The palladium was filtered off through a plug of diatomaceous earth and washed with EtOAc. The solvent was removed via rotary evaporation. The resulting residue was flash chromatographed (30% EtOAc/hexanes), providing N1-cyclohexylmethyl-N4-phenyl-benzene-1,2,4-triamine as a purple foam (0.04 g, 75.6% yield). M+, 294.

Workup

  1. customThe reaction flask was equipped with a septum
  2. filtrationThe palladium was filtered off through a plug of diatomaceous earth
  3. washwashed with EtOAc
  4. customThe solvent was removed via rotary evaporation
  5. customchromatographed (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9df3f190861a4029869deb1fb1acc50a
Source dataset
uspto-grants-2006_10
Patent number
US07115644B2

Reaction notes

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